JP2007254297A - Compound of light-emitting layer and organic electroluminescent device - Google Patents

Compound of light-emitting layer and organic electroluminescent device Download PDF

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JP2007254297A
JP2007254297A JP2006077013A JP2006077013A JP2007254297A JP 2007254297 A JP2007254297 A JP 2007254297A JP 2006077013 A JP2006077013 A JP 2006077013A JP 2006077013 A JP2006077013 A JP 2006077013A JP 2007254297 A JP2007254297 A JP 2007254297A
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emitting layer
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JP4823730B2 (en
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Takahiro Kai
Masaki Komori
Yuichi Sawada
Toshihiro Yamamoto
正樹 古森
敏浩 山本
雄一 澤田
孝弘 甲斐
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Nippon Steel Chem Co Ltd
新日鐵化学株式会社
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<P>PROBLEM TO BE SOLVED: To provide an organic EL (electroluminescent) device improving the emission efficiency of the device, sufficiently ensuring driving stability and having simple constitution. <P>SOLUTION: The organic EL device has a light-emitting layer between an anode and a cathode laminated onto a substrate. The light-emitting layer comprises a phosphorescence-emitting dopant and a compound of the light-emitting layer having a structure in which a diphenylfluorene skeleton represented by formula (1) is bonded to a carbazole skeleton with a linking group as a host material. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は新規な発光層化合物及び有機電界発光素子(以下、有機EL素子という)に関するものであり、詳しくは、燐光発光ドーパントと特定の構造を有するホスト化合物を併用することにより、高輝度を示す有機EL素子に関するものである。 The present invention relates to a novel luminescent layer compounds and organic electroluminescent device (hereinafter, referred to as organic EL device) is related to, particularly, the combined use of a host compound having a specific structure and the phosphorescent dopant, exhibits a high luminance the present invention relates to an organic EL element.

一般に、有機EL素子は、その最も簡単な構造としては発光層及び該層を挟んだ一対の対向電極から構成されている。 In general, the organic EL element is composed of a pair of counter electrodes sandwiching the light emitting layer and said layer as its simplest structure. 即ち、有機EL素子では、両電極間に電界が印加されると、陰極から電子が注入され、陽極から正孔が注入され、これらが発光層において再結合エネルギー準位が伝導帯から価電子帯に戻る際にエネルギーとして光を放出する現象を利用する。 That is, in the organic EL element, an electric field is applied between the electrodes, electrons from the cathode are injected, the holes injected from the anode, it is recombination energy level in the light-emitting layer valence band from the conduction band utilizing the phenomenon that emits light as energy when returning to.

近年、有機薄膜を用いたEL素子の開発が行われるようになった。 Recently the development of EL elements using an organic thin film is carried out. 特に発光効率を高めるため、電極からキャリアー注入の効率向上を目的として電極の種類の最適化を行い、芳香族ジアミンからなる正孔輸送層と8−ヒドロキシキノリンアルミニウム錯体(以下、Alq3という)からなる発光層とを電極間に薄膜として設けた素子の開発により、従来のアントラセン等の単結晶を用いた素子と比較して大幅な発光効率の改善がなされたことから、自発光・高速応答性といったと特徴を持つ高性能フラットパネルへの実用を目指して進められてきた。 Especially to enhance the luminous efficiency, optimizes the types of electrodes for the purpose of improving the efficiency of injecting carriers from the electrode, a hole transport layer comprising an aromatic diamine with 8-hydroxyquinoline aluminum complex (hereinafter, referred to as Alq3) consisting the development of device having a light emitting layer as a thin film between the electrodes, as compared to the device using a single crystal, such as a conventional anthracene from the significant improvement in luminous efficiency has been made, such as self emission and quick response with the aim of practical use to the high-performance flat panel with the features and has been promoted.

また、素子の発光効率を上げる試みとして、蛍光ではなく燐光を用いることも検討されている。 In another effort to enhance the luminous efficiency of the device, it has also been studied the use of phosphorescence in place of fluorescence. 上記の芳香族ジアミンからなる正孔輸送層とAlq3からなる発光層とを設けた素子をはじめとした多くの素子が蛍光発光を利用したものであったが、燐光発光を用いる、すなわち、三重項励起状態からの発光を利用すれば、従来の蛍光(一重項)を用いた素子と比べて、3倍程度の効率向上が期待される。 Many devices that including device provided with a light emitting layer made of a hole transport layer and Alq3 composed of an aromatic diamine described above were those using fluorescence emission, using phosphorescent, i.e., triplet by using the light emission from the excited state, as compared to devices using conventional fluorescence (singlet), to enhance the luminous efficiency approximately three times is expected. この目的のためにクマリン誘導体やベンゾフェノン誘導体を発光層とすることが検討されてきたが、極めて低い輝度しか得られなかった。 It has been studied the use of coumarin derivatives and benzophenone derivatives for this purpose and the light-emitting layer, was only very low luminance. その後、三重項状態を利用する試みとして、ユーロピウム錯体を用いることが検討されてきたが、これも高効率の発光には至らなかった。 Then, an attempt to utilize triplet state, although the use of a europium complex has been investigated, which also failed to emit light at high efficiency. この燐光発光を利用した研究は、燐光発光ドーパントとしては、特許文献1に挙げられるようなイリジウム錯体等の有機金属錯体を中心に研究が多数行われている。 Studies using this phosphorescence, the phosphorescent dopant are carried out studies a number around the organometallic complexes such as iridium complexes, such as those mentioned in Patent Document 1.

特表2003-515897号公報 JP-T 2003-515897 JP 特開2001-313178号公報 JP 2001-313178 JP 特開2002-352957号公報 JP 2002-352957 JP 特許第3079909号公報 Patent No. 3079909 Publication 特開2005-104971号公報 JP 2005-104971 JP 特開2005-213188号公報 JP 2005-213188 JP

一方、実用性のある発光層とするためには、ドーパント材料とホスト材料の組み合わせが重要であり、このようなホスト材料として提案されているのは、特許文献2で紹介されているカルバゾール化合物のCBPが挙げられる。 Meanwhile, in order to a practical light-emitting layer, the combination of the dopant material and the host material is important, what is proposed as such a host material, a carbazole compound is introduced in Patent Document 2 CBP and the like. 緑色燐光発光材料のトリス(2-フェニルピリジン)イリジウム錯体(以下、Ir(ppy)3という)のホスト材としてCBPを用いると、CBPは正孔を流し易く電子を流しにくい特性上、電荷注入バランスが崩れ、過剰の正孔は電子輸送側に流出し、結果としてIr(ppy)3からの発光効率が低下する。 Green tris (2-phenylpyridine) of phosphorescent material iridium complex (hereinafter, Ir (ppy) of 3) is used CBP as the host material, CBP is difficult characteristics on which shed easily electrons flowing hole, charge injection balance collapses, the excess holes to flow out to the electron transport side, the luminous efficiency from the results as Ir (ppy) 3 drops.

また、特許文献3で開示されている3-フェニル-4-(1'-ナフチル)-5-フェニル-1,2,4-トリアゾール(以下、TAZという)も燐光有機EL素子のホスト材として提案されているが、電子を流しやすく正孔を流しにくい特性上、発光領域が正孔輸送層側となる。 The proposal disclosed in Patent Document 3 3-phenyl-4- (1'-naphthyl) -5-phenyl-1,2,4-triazole (hereinafter, referred to as TAZ) as a host material for a phosphorescent organic EL device has been, on the hard characteristic flowing easily holes flowing electrons, the light emitting region becomes the hole transport layer side. したがって、正孔輸送層の材料によってはIr(ppy)3との相性問題により、Ir(ppy)3からの発光効率が低下することも考えられる。 Thus, depending on the material of the hole transport layer by compatibility problems with Ir (ppy) 3, also conceivable that the luminous efficiency from Ir (ppy) 3 drops. 例えば、正孔輸送層として高性能、高信頼性、高寿命の点から最も良く使用されている4,4'-ビス(N-(1-ナフチル)-N-フェニルアミノ)ビフェニル(以下、NPBという)は、Ir(ppy)3との相性が悪く、Ir(ppy)3からNPBにエネルギー遷移が起き、発光効率が低下するという問題がある。 For example, high performance as a hole transport layer, high reliability, best is used 4,4'-bis terms of long life (N-(1-naphthyl) -N- phenylamino) biphenyl (hereinafter, NPB ) that has poor compatibility with Ir (ppy) 3, occurs energy transition from Ir (ppy) 3 to NPB, luminous efficiency is lowered.

更に、特許文献4〜6でフルオレン化合物が数多く開示されているが、特許文献4と6ではビスフェニルフルオレン化合物のフェニル部位にカルバゾール基が直接結合した化合物を開示するのみであり、連結基を介してカルバゾール基が結合した化合物の有用性を開示するものではない。 Further it is disclosed fluorene compound number in Patent Document 4 to 6, only a carbazole group on the phenyl portion of the patent document 4, and 6 bisphenyl fluorene compound disclosed the compound bound directly, via a linking group It does not have a carbazole group discloses the utility of compounds bound Te. 連結基を介してカルバゾール置換芳香族化合物を結合させることで、高い三重項エネルギーを有するホスト材料となる。 Through a linking group by coupling the carbazole-substituted aromatic compound, a host material having a high triplet energy. また、特許文献5においてはカルバゾール基が直接又は連結基を介して、フルオレン化合物に2個置換する化合物を開示しているが、カルバゾール基が3個以上置換した化合物の有用性を示すものではない。 Also, through a carbazole group directly or a linking group in the patent document 5 discloses a compound that replaces two fluorene compound, a carbazole group it is not intended to demonstrate the utility of three or more substituted compounds . 3個以上のカルバゾール基を置換することにより、熱的安定性が向上し、高効率かつ高い駆動安定性が期待できる。 By substituting three or more carbazole groups, improved thermal stability, high efficiency and high driving stability can be expected.

有機EL素子をフラットパネル・ディスプレイ等の表示素子に応用するためには、素子の発光効率を改善すると同時に駆動時の安定性を十分に確保する必要がある。 In order to apply the organic EL devices to display devices such as flat panel displays, it is necessary to ensure sufficient stability during driving while improving the luminous efficiency of the device. 本発明は、上記現状に鑑み、高効率かつ高い駆動安定性を有した実用上有用な有機EL素子及びそれに適する化合物を提供することを目的とする。 The present invention aims at providing the current view of the high efficiency and high driving had stability practically useful organic EL elements and compounds suitable for it.

本発明者らは、鋭意検討した結果、特定構造のビスフェニルフルオレン化合物を有機EL素子の発光層化合物に使用することで、上記課題を解決することができることを見出し、本発明を完成するに至った。 The present inventors have made intensive studies, as a result, to use a bisphenyl fluorene compound having a specific structure in the light emitting layer compound of the organic EL device, it found that it is possible to solve the above problems, thereby completing the present invention It was.

本発明は、下記一般式(1)で表される発光層化合物である。 The present invention is a light-emitting layer compound represented by the following general formula (1).
(式中、Ar 1は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基からなる二価の連結基を表し、Xは酸素原子、硫黄原子、カルボニル基、カルボニルオキシ基、置換基を有してもよいアミド基又はスルホニル基を表し、Rは水素、炭素数1〜4のアルキル基又は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基を表わし、複数のAr 1又はRは同一であっても異なっていても良い。m、nは1又は2の整数を表す。) (In the formula, Ar 1 represents an aromatic condensed ring carbon atoms of the structural non-substituted or unsubstituted 4-18 hydrocarbon group or an aromatic divalent linking group comprising a heterocyclic group, X is an oxygen atom, a sulfur atom , carbonyl group, carbonyloxy group, which may have a substituent represents an amide group or a sulfonyl group, R represents hydrogen, 4 carbon substituted or unsubstituted non-alkyl group or a condensed ring structure having from 1 to 4 carbon atoms 18 represents an aromatic hydrocarbon group or an aromatic heterocyclic group, the plurality of Ar 1 or R may be different even in the same .m, n is an integer of 1 or 2.)

また、本発明は、下記一般式(2)で表される発光層化合物である。 Further, the present invention is a light-emitting layer compound represented by the following general formula (2).
(式中、Ar 1は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基からなる二価の連結基を表し、Xは直接結合を表し、Rは水素、炭素数1〜4のアルキル基又は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基を表わし、複数のAr 1又はRは同一であっても異なっていても良い。m、nは1又は2の整数を表し、m+nは3又は4である。) (In the formula, Ar 1 represents an aromatic hydrocarbon group or aromatic divalent linking group comprising a heterocyclic group condensed carbon structure is not substituted or unsubstituted 4 to 18, X represents a direct bond, R represents hydrogen, an aromatic hydrocarbon group or an aromatic heterocyclic group having 4 to 18 carbon atoms substituted or unsubstituted non-alkyl group or a condensed ring structure having from 1 to 4 carbon atoms, the plurality of Ar 1 or R identical may even be different also .m, n represents an integer of 1 or 2, m + n is 3 or 4.)

また、本発明は、下記一般式(3)で表される発光層化合物である。 Further, the present invention is a light-emitting layer compound represented by the following general formula (3).
(式中、Ar 1 、X及びRは、一般式(1)と同じである。m、nは1又は2の整数を表し、m+nは3又は4である) (Wherein, Ar 1, X and R are the same as the general formula (1) .m, n represents an integer of 1 or 2, m + n is 3 or 4)

また、本発明は、下記一般式(4)で表される発光層化合物である。 Further, the present invention is a light-emitting layer compound represented by the following general formula (4).
(式中、Rは、一般式(1)と同じである。Xは酸素、硫黄原子を表す。) (Wherein, R is the same as the general formula (1) .X represents oxygen, sulfur atom.)

更に本発明は、基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと上記いずれかの発光層化合物をホスト材料として含有することを特徴とする有機電界発光素子である。 The invention further between an anode and a cathode laminated on a substrate, an organic electroluminescent device having a light-emitting layer, the light emitting layer, a phosphorescent dopant and the one of the light-emitting layer compound host materials an organic electroluminescent device characterized by containing as.

また本発明は、陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有してなる上記有機電界発光素子である。 The present invention is the organic electroluminescent device comprising an electron injecting and transporting layer between the hole injection transport layer and a cathode and a light emitting layer between the anode and the light emitting layer. 更に本発明は、発光層と電子注入輸送層の間に正孔阻止層を有してなる上記有機電界発光素子である。 The present invention is the organic electroluminescent device comprising a hole blocking layer between the light-emitting layer and the electron injection transport layer.

本発明の発光層化合物は前記一般式(1)〜(4)で表わされる化合物のいずれかである。 Luminescent layer compounds of the invention are any of the compounds represented by the general formula (1) to (4). 本発明の発光層化合物は、2以上組合わせて使用することもできる。 Luminescent layer compounds of the present invention can also be used in combination of two or more.
一般式(1)、(3)及び(4)で表わされる化合物は、ビスフェニルフルオレン化合物のフェニル部位に酸素原子、硫黄原子、カルボニル基等の二価の連結基を介して、カルバゾール置換芳香族化合物を結合させることで、分子骨格の共役性を低下させ、高い三重項エネルギーを有する高効率かつ高い駆動安定性を有した実用上有用な有機EL素子を提供することができる。 Formula (1), (3) and (4) a compound represented by an oxygen atom to the phenyl part of bisphenyl fluorene compound, a sulfur atom, via a divalent linking group such as a carbonyl group, a carbazole-substituted aromatic by binding the compound to reduce the conjugation of the molecular skeleton, it is possible to provide a highly efficient and practically useful organic EL device having high driving stability with high triplet energy. また、一般式(2)及び(3)で表わされる化合物は、カルバゾール置換基を3個以上結合させることで、より高い安定性を達成できる。 Moreover, the compound represented by the general formula (2) and (3), by coupling the carbazole substituents three or more, can achieve a higher stability.

一般式(1)〜(3)において、Ar 1は好ましくは、次のような基である。 In the general formula (1) ~ (3), Ar 1 is preferably as follows groups.
ベンゼン環、ビフェニル環、ターフェニル環、フラン環、チオフェン環、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環、トリアジン環などから生ずる2価の芳香族炭化水素基又は芳香族複素環基であり、単環構造のみを有しており、カルバゾール環との共役系を広げない点で共通する。 A benzene ring, a biphenyl ring, a terphenyl ring, a furan ring, a thiophene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring divalent aromatic arising from such hydrocarbon group or an aromatic heterocyclic group, It has only single ring structures, common in that they do not spread the conjugated system of the carbazole ring.

一般式(1)及び(3)において、Xは好ましくは、次のような基である。 In the general formula (1) and (3), X is preferably, as follows groups.
酸素原子、硫黄原子、カルボニル基、カルボニルオキシ基、N−フェニルアミド基又はスルホニル基であり、ビフェニルフルオレン化合物のフェニル基とカルバゾール置換芳香族との共役系を切ることができる構造を有する点で共通する。 Oxygen atom, a sulfur atom, a carbonyl group, a carbonyloxy group, an N- phenyl amide group or a sulfonyl group, common in that it has a structure that can cut a conjugated system with a phenyl group and a carbazole substituted aromatic biphenyl fluorene compound to.

一般式(1)〜(4)において、Rは好ましくは、次のような基である。 In the general formula (1) ~ (4), R is preferably similar to the following groups.
メチル、エチル、n-プロピル、2-プロピル、n-ブチル、イソブチル、tert-ブチル等の炭素数1〜4のアルキル基、ベンゼン環、ビフェニル環、ターフェニル環、フラン環、チオフェン環、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環、トリアジン環などから生ずる1価の基であり、電気的な酸化還元に強く、熱的安定性に優れている点で共通する。 Methyl, ethyl, n- propyl, 2-propyl, n- butyl, isobutyl, alkyl group having 1 to 4 carbon atoms such as tert- butyl, a benzene ring, a biphenyl ring, a terphenyl ring, a furan ring, a thiophene ring, a pyridine ring a pyrazine ring, a pyridazine ring, a pyrimidine ring, a monovalent group resulting from triazine ring, strongly electrical redox, common at the point of excellent thermal stability.

一般式(1)〜(4)において、複数のX、Ar 1及びRがある場合、これらは同一であっても、異なってもよい。 In formulas (1) to (4), if there are multiple X, Ar 1 and R, these may be the same or different. しかし、これらの化合物を合成する上では、対応する位置のX、Ar 1及びRは同じ基であることが有利である。 However, in order to synthesize these compounds, X in the corresponding positions, Ar 1 and R are advantageously the same group.

一般式(1)で表される化合物の合成法の一つとしては、対応するフルオレン誘導体と対応するハロゲン化フェニルカルバゾールを、有機溶媒中又は無溶媒で、塩基及び触媒の存在下、窒素雰囲気下、100〜200℃程度の温度で、1〜90時間程度反応させて得ることができる。 As one of the general formulas synthesis of the compound represented by (1), a halogenated phenyl carbazole and the corresponding corresponding fluorene derivative, in an organic solvent or without solvent in the presence of a base and a catalyst, under a nitrogen atmosphere can be at a temperature of about 100 to 200 ° C., obtained by reacting about 1 to 90 hours. ハロゲン化フェニルカルバゾールのハロゲン原子としては、塩素、臭素、よう素等が挙げられる。 The halogen atom of the halogenated phenyl carbazole, chlorine, bromine, iodine and the like. 使用される塩基としては、炭酸カリウム、炭酸ナトリウム、炭酸セシウム、リン酸カリウム、水酸化リチウム、水酸化ナトリウム、ナトリウム tert-ブトキシド、カリウム tert-ブトキシドのような無機塩基、ピリジン、ピコリン、トリエチルアミンのような有機塩基が挙げられる。 The base used, potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate, lithium hydroxide, sodium hydroxide, sodium tert- butoxide, inorganic bases such as potassium tert- butoxide, pyridine, picoline, as triethylamine organic bases and the like such. 触媒としては、銅粉、酸化銅、ハロゲン化銅、硫酸銅等の銅系触媒、又は酢酸パラジウム、ビス(ジベンジリデンアセトン)パラジウムなどのパラジウム源と、トリtert-ブチルホスフィンなどの配位子により形成されるパラジウム錯体系触媒が挙げられる。 As the catalyst, copper powder, copper oxide, copper halide, copper-based catalyst such as copper sulfate, or palladium acetate, and palladium source such as bis (dibenzylideneacetone) palladium, a ligand such as tri-tert- butylphosphine palladium complex catalyst which is formed and the like. 溶媒は、原料を溶解して、反応を行わせることができるものであればよい。 The solvent dissolves the raw materials, as long reaction as it can perform. 例えば、トルエン、キシレン、ジオキサン、テトラリン、キノリン、ニトロベンゼン、ジメチルスルフォキシド、N、N-ジメチルホルムアミド等の溶媒が挙げられる。 For example, toluene, xylene, dioxane, tetralin, quinoline, nitrobenzene, dimethyl sulfoxide, N, include solvents such as N- dimethylformamide.

反応終了後、水を加えて有機層を分離し、これを濃縮し、酢酸エチル等の低沸点溶媒で洗浄し、減圧乾燥することにより、本発明の化合物を得る。 After completion of the reaction, the organic layer was separated by adding water, which was concentrated and washed with a low boiling solvent such as ethyl acetate, and dried under reduced pressure to give the compound of the present invention. 本発明の化合物を有機EL材料の発光層化合物、特にホスト材料としての性能を高めるためには、更に昇華精製することが好ましい。 Compound luminescent layer compound in the organic EL material of the present invention, particularly to enhance the performance of the host material is preferably further purified by sublimation.

次に、一般式(1)〜(4)で表される化合物の好ましい具体例を以下に示すが、これらに限定するものではない。 Next, the general formula (1) to Specific preferred examples of the compound represented by formula (4) below, not limited thereto. なお、化学式の下に記載された番号は化合物番号である。 The numbers listed under the formula is a compound number.

発光層における燐光発光ドーパント材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金属錯体を含有するものがよい。 The phosphorescent dopant material in the emitting layer, ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, good those containing organic metal complex containing at least one metal selected from platinum and gold. かかる有機金属錯体は、前記特許文献等で公知であり、これらが選択されて使用可能である。 Such organic metal complexes are the known in patent literature like, and can be selected from them and used.

好ましい燐光発光ドーパントとしては、Ir等の貴金属元素を中心金属として有するIr(ppy)3等の錯体類、Ir(bt)2・acac3等の錯体類、PtOEt3等の錯体類が挙げられる。 Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element of Ir such as the central metal, Ir (bt) complexes such as 2 · acac3, include complexes such as PtOEt3. これらの錯体類の具体例を以下に示すが、下記の化合物に限定されない。 Specific examples of these complexes are shown below, but are not limited to the following compounds.

前記燐光発光ドーパントが発光層中に含有される量は、5〜10重量%の範囲にあることが好ましい。 The amount of the phosphorescent dopant is contained in the light-emitting layer is preferably in the range of 5 to 10 wt%.

次に、本発明の発光層化合物を用いた、有機EL素子について説明する。 Next, the light-emitting layer compound of the present invention is used, the organic EL device will be described.

本発明の有機EL素子は、基板上に積層された陽極と陰極の間に、少なくとも1つの発光層を有する有機EL素子であり、該発光層が燐光発光性ドーパントと、一般式(1)〜(4)で表わされる化合物を含有することを特徴とする。 The organic EL device of the present invention, between an anode and a cathode laminated on a substrate, an organic EL element having at least one light emitting layer, and the light emitting layer is phosphorescent dopant, the general formula (1) to characterized in that it contains a compound represented by (4).
そして、好ましい有機EL素子の構造としては、陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有した構造や発光層と電子注入輸送層の間に正孔阻止層を有してなる構造がある。 And, as the structure of the preferred organic EL element, between the structure and the light emitting layer and the electron injection transport layer having an electron injecting and transporting layer between the hole injection transport layer and a cathode and a light emitting layer between the anode and the light-emitting layer there is structure has a hole blocking layer.

次に、本発明の有機EL素子の構造について、図面を参照しながら説明するが、本発明の有機EL素子の構造は何ら図示のものに限定されるものではない。 Next, the structure of the organic EL device of the present invention will be described with reference to the drawings, the structure of the organic EL device of the present invention is in no way limited to the illustrated.

図1は本発明に用いられる一般的な有機EL素子の構造例を模式的に示す断面図であり、1は基板、2は陽極、3は正孔注入層、4は正孔輸送層、5は発光層、6は電子輸送層、7は陰極を各々表わす。 Figure 1 is a sectional view showing a structural example of a general organic EL element used in the present invention schematically, 1 denotes a substrate, 2 anode, 3 hole-injecting layer, 4 hole-transporting layer, 5 the light-emitting layer, 6 electron-transporting layer, 7 represents each cathode. 本発明の有機EL素子では、基板、陽極、発光層及び陰極を必須の層として有するが、必須の層以外の層以外に、正孔注入輸送層、電子注入輸送層を有することがよく、更に発光層と電子注入輸送層の間に正孔阻止層を有することがよい。 In the organic EL device of the present invention includes a substrate, an anode has a light-emitting layer and a cathode as essential layers, in addition to a layer other than the essential layers, the hole injection transport layer, and an electron-injecting and transporting layer, further it is possible to have a hole blocking layer between the light-emitting layer and the electron injection transport layer. なお、正孔注入輸送層は、正孔注入層と正孔輸送層のいずれか又は両者を意味し、電子注入輸送層は、電子注入層と電子輸送層のいずれか又は両者を意味する。 Incidentally, the hole injecting and transporting layer means one or both of the hole injection layer and a hole transport layer, an electron injection transport layer is meant either or both of the electron injection layer and the electron transport layer.

なお、図1とは逆の構造、すなわち、基板1上に陰極7、電子輸送層6、発光層5、正孔輸送層4、陽極2の順に積層することも可能であり、既述したように少なくとも一方が透明性の高い2枚の基板の間に本発明の有機EL素子を設けることも可能である。 Incidentally, the reverse of the structure to the FIG. 1, i.e., the cathode 7 on the substrate 1, an electron transport layer 6, the light emitting layer 5, a hole transport layer 4, it is also possible to laminate in the order of the anode 2, as already described it is also possible to provide at least one of the organic EL device of the present invention during the high two substrates transparent to. この場合も、必要により層を追加したり、省略したりすることが可能である。 Again, adding layers as needed, it is possible or omitted.

本発明は、有機EL素子が、単一の素子、アレイ状に配置された構造からなる素子、陽極と陰極がX−Yマトリックス状に配置された構造のいずれにおいても適用することができる。 The present invention relates to an organic EL element is a single element, it can also be applied in any device consisting of its structure arranged in array, an anode and a cathode of the deployed structure onto the X-Y matrix. 本発明の有機EL素子によれば、発光層に特定の骨格を有する化合物と、燐光発光ドーパントを含有させることにより、従来の一重項状態からの発光を用いた素子よりも発光効率が高くかつ駆動安定性においても大きく改善された素子が得られ、フルカラーあるいはマルチカラーのパネルへの応用において優れた性能を発揮できる。 According to the organic EL device of the present invention, a compound having a specific skeleton to the light emitting layer, by containing a phosphorescent dopant, high luminous efficiency and driving than devices using light emission from conventional singlet state obtained large improved device also in stability, it can exhibit excellent performance in applications to full-color or multicolor panels.

以下、本発明につき、実施例によって更に詳しく説明するが、本発明は勿論、これらの実施例に限定されるものではなく、その要旨を越えない限りにおいて、種々の形態で実施することが可能である。 Hereinafter, the present invention will be described examples in more detail, the present invention is of course not limited to these Examples, as long as not exceeding the gist can be implemented in various forms is there.

実施例1 Example 1
化合物1の合成 脱気窒素置換した500ml三口フラスコに9-(ビス(p-ヒドロキシフェニル))フルオレン(BPFL) 5.43g(15.40 mmol)、p-ヨードフェニルカルバゾール 15.00g(40.43 mmol)、ヨウ化銅2.98g(15.65 mmol)、N,N'−ジメチルグリシン塩酸塩 3.00g(21.49 mmol)、炭酸セシウム 16.40 g(50.33 mmol)、を加え、これに1,4-ジオキサン 300 mlを加えて攪拌させた。 Compound 1 of synthesis had been deaerated and filled with nitrogen were 500ml three-necked flask 9- (bis (p- hydroxyphenyl)) fluorene (BPFL) 5.43g (15.40 mmol), p- iodophenyl carbazole 15.00 g (40.43 mmol), copper iodide 2.98g (15.65 mmol), N, N'- dimethyl glycine hydrochloride 3.00 g (21.49 mmol), cesium carbonate 16.40 g (50.33 mmol), was added and allowed to stir and added with 1,4-dioxane 300 ml . その後120℃まで加熱し、72時間攪拌した。 Then heated to 120 ° C., and stirred for 72 hours. 室温まで冷却した後、反応溶液を濾過し、溶媒を減圧留去した。 After cooling to room temperature, the reaction solution was filtered, and the solvent was evaporated under reduced pressure. 得られた茶色粉末19gを活性炭で処理した後、シリカゲルクロマトグラフィーで精製して白色固体14.36g(収率89.2%)を得た。 The resulting brown powder 19g and treated with activated charcoal, to give a white solid 14.36 g (89.2% yield) was purified by silica gel chromatography.
化合物1のFD−MS(M+)は832、融点は169℃であった。 Of Compound 1 FD-MS (M +) 832 and a melting point of 169 ° C..

実施例2 Example 2
化合物14の合成 窒素雰囲気下、200ml三口フラスコに無水N,N'-ジメチルホルムアミド中で水素化ナトリウム(55%)17g(0.39 mol)をカルバゾール71 g(0.43 mol)に作用させた後、1-ブロモ-3,5-ジフルオロベンゼン25g(0.13 mol)を添加し、80℃で10時間、120℃で0.5時間、140℃で1時間攪拌した。 Under nitrogen atmosphere compound 14, anhydrous 200ml three-necked flask N, N'-dimethylformamide sodium hydride in (55%) was allowed to act on 17 g (0.39 mol) of carbazole 71 g (0.43 mol), 1- It was added bromo-3,5-difluorobenzene 25g (0.13 mol), 10 hours at 80 ° C., 0.5 hours at 120 ° C., and stirred for 1 hour at 140 ° C.. 得られた溶液に水1000ml、メタノール300mlを加えて、濾過した。 The resulting solution in water 1000 ml, by adding methanol 300 ml, and filtered. 得られた固体を水500mlを用いて3回、メタノール500mlを用いて3回洗浄した。 The resulting solid with water 500 ml three times, then washed 3 times with methanol 500 ml. その後、THFとメタノールにより晶析を行い、1-ブロモ-3,5-ビス(N-カルバゾリル)ベンゼン32g(収率58.3%)を得た。 Thereafter, crystallization with THF and methanol, to give 1-bromo-3,5-bis (N- carbazolyl) benzene 32 g (58.3% yield).

窒素雰囲気下、1000ml三口フラスコに無水THF100ml、マグネシウム1.46g(60mmol)を仕込み、THF還流下、1-ブロモ-3,5-ビス(N-カルバゾリル)ベンゼン24.3g(50.0mmol)のTHF220ml溶液をゆっくりと滴下した。 Under a nitrogen atmosphere, anhydrous 1000ml three-necked flask 100 ml of THF, was charged with magnesium 1.46 g (60 mmol), THF under reflux, 1-bromo-3,5-bis (N- carbazolyl) THF220ml solution of benzene 24.3 g (50.0 mmol) slowly It was dropped with. 2時間後、室温まで冷却し、得られた溶液を、0℃下でトリメトキシボラン6.23g(60.0mmol)のTHF150ml溶液に滴下し、1時間攪拌した。 After 2 hours, then cooled to room temperature and the resulting solution was added dropwise to THF150ml solution of trimethoxy borane 6.23 g (60.0 mmol) under 0 ° C., and stirred for 1 hour. その後、メタノールと塩酸を加え、12時間攪拌した。 Thereafter, methanol and hydrochloric acid was added, and the mixture was stirred for 12 hours. 得られた溶液を濾別し、酢酸エチルと水を用いて洗浄した。 The resulting solution was filtered off and washed with ethyl acetate and water. 有機層と水層に分け、硫酸マグネシウムで乾燥後、溶媒を減圧留去した。 Divided into an organic layer and an aqueous layer, dried over magnesium sulfate and evaporated under reduced pressure. 得られた固体をシリカゲルクロマトグラフィーで精製し、3,5−ビスカルバゾリルフェニルボロン酸を14.6g(収率64.5%)得た。 The resulting solid was purified by silica gel chromatography, 3,5-bis-carbazolyl phenylboronic acid to give 14.6 g (64.5% yield).

500ml三口フラスコに9-(ビス(p-ヨードフェニル))フルオレン 10.7g(15mmol)、3,5−ビスカルバゾリルフェニルボロン酸 13.9g(32.5mmol)、テトラキストリフェニルホスフィンパラジウム1.73g(1.5mmol)、2M−炭酸ナトリウム水溶液30mlを加え、これにトルエン150mlを加えて攪拌させた。 To 500ml three-necked flask 9- (bis (p- iodophenyl)) fluorene 10.7 g (15 mmol), 3,5-bis carbazolylphenyl acid 13.9 g (32.5 mmol), tetrakistriphenylphosphine palladium 1.73 g (1.5 mmol ), added 2M- sodium carbonate aqueous solution 30 ml, and this was stirred with toluene 150 ml. その後90℃まで加熱し、3.5時間攪拌した。 Then heated to 90 ° C., and stirred for 3.5 hours. 室温まで冷却した後、反応溶液を濾過し、溶媒を減圧留去した。 After cooling to room temperature, the reaction solution was filtered, and the solvent was evaporated under reduced pressure. 得られた茶色粉末30.5gを活性炭で処理した後、シリカゲルクロマトグラフィーを行い、得られた固体をトルエン−ヘキサンを用いて晶析を行うことで白色固体9.9g(収率58.4%)を得た。 The resulting brown powder 30.5g was treated with activated carbon, chromatographed on silica gel, the resulting solid with toluene - to give a white solid 9.9g by performing crystallization with hexane (58.4% yield) .
化合物14のFD−MS(M+)は1130、融点は381℃であった。 FD-MS of Compound 14 (M +) 1130 and a melting point of 381 ° C..

実施例3 Example 3
ガラス基板上に真空蒸着法にて、真空度4.0×10 -4 Pa の条件にて化合物1とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %であるような薄膜を1.0Å/秒にて50nmの厚さで形成した。 On a glass substrate by vacuum deposition, and evaporation from compound 1 and Ir (ppy) 3 and a different evaporation sources at a vacuum degree of 4.0 × 10 -4 Pa conditions, Ir (ppy) 3 concentrations 7.0% It was formed to a thickness of 50nm certain such thin films at 1.0 Å / sec.
作成した薄膜を、蛍光測定装置にて評価した。 A thin film that was created, was evaluated by fluorescence measurement device. 励起波長は化合物1の極大吸収波長であり、そのときに出てくる光を観察した。 The excitation wavelength was the maximum absorption wavelength of compound 1 was observed light emerging at that time. 結果を表1に示す。 The results are shown in Table 1.

実施例4 Example 4
ホスト材料として化合物14を用いた以外は実施例3と同様にして薄膜を作成し、作成した薄膜を、蛍光測定装置にて評価した。 Except for using the compound 14 as a host material in the same manner as in Example 3 to form a thin film, the thin film produced was evaluated by fluorescence measurement device. 励起波長は化合物14の極大吸収波長であり、そのときに出てくる光を観察した。 The excitation wavelength was the maximum absorption wavelength of compound 14 was observed light emerging at that time. 結果を表1に示す。 The results are shown in Table 1.

比較例1 Comparative Example 1
薄膜主成分をAlq3に変えて薄膜を作成した以外は、実施例3と4と同様に行った。 Except that a thin film by changing the film main component Alq3 was performed in the same manner as in Example 3 and 4. 結果を表1に示す。 The results are shown in Table 1.

発光層の主たる材料に化合物1又は化合物14を用いた場合は、Ir(ppy)3にエネルギーが遷移し、Ir(ppy)3からの発光が観察されるが、Alq3を用いた場合は、Ir(ppy)3にエネルギーが遷移せず、Alq3自身が蛍光を発することがわかる。 If the primary material of the light-emitting layer using the compound 1 or compound 14, when the energy transitions to Ir (ppy) 3, although light emission from Ir (ppy) 3 is observed, using Alq3 is, Ir (ppy) energy does not transition to 3, Alq3 itself seen to fluoresce.

実施例5 Example 5
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。 In Figure 1, omitting the hole injection layer, thereby constructing an organic EL device of the added forming the electron injection layer. 膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10 -4 Paで積層させた。 On a glass substrate anode made of thickness 150nm of ITO was formed, the respective thin films by vacuum vapor deposition, are stacked in a vacuum of 4.0 × 10 -4 Pa. まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。 First, NPB as a hole transport layer was formed to a thickness of 60nm on the ITO.
次に、正孔輸送層上に、発光層として化合物1とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。 Next, on the hole transport layer, the compound 1 and Ir (ppy) 3 and different deposition sources as the light emitting layer by co-evaporation, was formed to a thickness of 25 nm. この時、Ir(ppy)3の濃度は7.0 %であった。 At this time, the concentration of Ir (ppy) 3 was 7.0%. 次に、電子輸送層としてAlq3を50nmの厚さに形成した。 Next, to form an Alq3 as an electron-transporting layer to a thickness of 50nm. 更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。 Further, the electron transport layer, lithium fluoride (LiF) was formed to a thickness of 0.5nm as an electron injection layer. 最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。 Finally, on the electron injection layer, aluminum (Al) was formed to a thickness of 170nm as an electrode, thereby constructing an organic EL device.

実施例6 Example 6
発光層として化合物14を用いた以外は実施例5と同様にして有機EL素子を作成した。 Except for using the compound 14 as a light-emitting layer An organic EL device was fabricated in the same manner as in Example 5.

得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、表2のような発光特性を有することが確認された。 When the obtained organic EL device was connected to an outside power source, it was confirmed that the light emission characteristics shown in Table 2. 表2において、輝度、電圧及び発光効率は、10mA/cm 2での値を示す。 In Table 2, the luminance, voltage, and luminous efficiency were measured at 10 mA / cm 2. なお、素子発光スペクトルの極大波長は517 nmであり、Ir(ppy)3からの発光が得られていることがわかった。 Incidentally, maximum wavelength of the element emission spectrum was 517 nm, it was found that light emission from Ir (ppy) 3 is obtained.

比較例2 Comparative Example 2
正孔輸送層としてHMTPDを、発光層の主成分としてTAZを用いた以外は実施例5と同様にして有機EL素子を作成した。 The HMTPD as a hole transport layer, except for using TAZ as the main component of the light-emitting layer An organic EL device was fabricated in the same manner as in Example 5.

比較例3 Comparative Example 3
発光層の主成分として、TAZを用いた以外は実施例5と同様にして有機EL素子を作成した。 As a main component of the light-emitting layer An organic EL device was fabricated except using TAZ in the same manner as in Example 5.

比較例4 Comparative Example 4
比較例3において、発光層のホスト材料としてTAZの代わりに、特許第3079909号公報に記載の下記化合物を用いた以外は実施例5と同様にして有機EL素子を作成した。 In Comparative Example 3, in place of the TAZ as a host material of a light-emitting layer An organic EL device was fabricated except for using the following compound described in Japanese Patent No. 3,079,909 in the same manner as in Example 5.

本発明の有機EL素子は、低電圧において高輝度・高効率で発光させることが可能となる。 The organic EL device of the present invention, it is possible to emit light at low voltage with high luminance and high efficiency. 従って、本発明による有機EL素子はフラットパネル・ディスプレイ(例えばOAコンピュータ用や壁掛けテレビ)、車載表示素子、携帯電話表示や面発光体としての特徴を生かした光源(例えば、複写機の光源、液晶ディスプレイや計器類のバックライト光源)、表示板、標識灯への応用が考えられ、その技術的価値は大きいものである。 Therefore, the organic EL device according to the present invention is a flat panel display (e.g. OA computers use or wall-mounted television), vehicle display devices, light sources utilizing the characteristics as a mobile phone display or a surface light emitter (e.g., a copying machine the light source, the liquid crystal backlight sources for display or instrument), display panels, and a beacon light is considered, its technical value is larger.

有機EL素子の一例を示した模式断面図。 Schematic sectional view showing an example of the organic EL element.

符号の説明 DESCRIPTION OF SYMBOLS

1 基板、2 陽極、3 正孔注入層、4 正孔輸送層、5 発光層、6 電子輸送層、7 陰極 1 substrate, 2 anode, 3 hole-injecting layer, 4 hole-transporting layer, 5 light-emitting layer, 6 electron-transporting layer, 7 cathode

Claims (7)

  1. 下記一般式(1)で示される発光層化合物。 Emitting layer compound represented by the following general formula (1).
    (式中、Ar 1は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基からなる二価の基を表し、Xは酸素原子、硫黄原子、カルボニル基、カルボニルオキシ基、置換基を有してもよいアミド基又はスルホニル基を表し、Rは水素、炭素数1〜4のアルキル基、縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基を表わし、複数のAr 1又はRは同一であっても異なっていても良い。m、nは1又は2の整数を表す。) (In the formula, Ar 1 represents a divalent group consisting of an aromatic hydrocarbon group or an aromatic heterocyclic group condensed carbon structure is not substituted or unsubstituted 4 to 18, X is an oxygen atom, a sulfur atom, represents a carbonyl group, a carbonyloxy group, an optionally substituted amide group or a sulfonyl group, R represents hydrogen, an alkyl group, the number of carbon atoms of the substituted or unsubstituted non-condensed ring structure having from 1 to 4 carbon atoms from 4 to 18 It represents an aromatic hydrocarbon group or an aromatic heterocyclic group, the plurality of Ar 1 or R may be different even in the same .m, n is an integer of 1 or 2.)
  2. 下記一般式(2)で示される発光層化合物。 Emitting layer compound represented by the following general formula (2).
    (式中、Ar 1は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基からなる二価の基を表し、Xは直接結合を表し、Rは水素、炭素数1〜4のアルキル基又は縮環構造でない置換若しくは未置換の炭素数4〜18の芳香族炭化水素基又は芳香族複素環基を表わし、複数のAr 1又はRは同一であっても異なっていても良い。m、nは1又は2の整数であるが、m+nは3又は4である。) (In the formula, Ar 1 represents a divalent group consisting of an aromatic hydrocarbon group or an aromatic heterocyclic group condensed carbon structure is not substituted or unsubstituted 4 to 18, X represents a direct bond, R is hydrogen, an aromatic hydrocarbon group or an aromatic heterocyclic group having 4 to 18 carbon atoms substituted or unsubstituted non-alkyl group or a condensed ring structure having from 1 to 4 carbon atoms, a plurality of Ar 1 or R are identical may be different even .m, n is 1 or 2 is an integer, m + n is 3 or 4.)
  3. 下記一般式(3)で示される請求項1記載の発光層化合物。 Emitting layer compound according to claim 1 represented by the following general formula (3).
    (式中、m、nは1又は2の整数を表すが、m+nは3又は4である。Ar 1 、X及びRは、一般式(1)と同意である。) (Wherein, m, n is an integer of 1 or 2, .Ar 1 m + n is 3 or 4, X and R are as in formula (1) I agree.)
  4. 下記一般式(4)で示される請求項1記載の発光層化合物。 Emitting layer compound according to claim 1 represented by the following general formula (4).
    (式中、Xは酸素、硫黄原子を表し、Rは一般式(1)と同意である。) (Wherein, X is oxygen, a sulfur atom, R is the general formula (1) agree.)
  5. 基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと請求項1〜4のいずれかに記載の発光層化合物をホスト材料として含有することを特徴とする有機電界発光素子。 Between an anode and a cathode laminated on a substrate, an organic electroluminescent device having a light-emitting layer, the light emitting layer, a luminescent layer compound according to any one the phosphorescent dopant of claims 1 to 4 the organic electroluminescent device characterized by containing as a host material.
  6. 陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有してなる請求項5記載の有機電界発光素子。 The organic electroluminescent device comprising an electron injection transport layer according to claim 5, wherein between the hole injection transport layer and a cathode and a light emitting layer between the anode and the light emitting layer.
  7. 発光層と電子注入輸送層の間に正孔阻止層を有してなる請求項5又は6記載の有機電界発光素子。 The organic electroluminescent device comprising a hole blocking layer according to claim 5 or 6, wherein between the light-emitting layer and the electron injection transport layer.
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